CAS No.76-22-2,2-Bornanone Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	76-22-2
Name:	2-Bornanone
Article Data:	196

Formula:	C₁₀H₁₆O
Molecular Weight:	152.236
Synonyms:	1,7,7-Trimethylbicyclo[2.2.1]-2-heptanone;1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one;2-Bornanone;Bicyclo(2.2.1)heptan-2-one, 1,7,7-trimethyl-;2-Kamfanon;1,7,7-Trimethylnorcamphor;2-Camphanone;Bornane, 2-oxo-;DL-Camphor;Norcamphor, 1,7,7-trimethyl-;DL-Bornan-2-one;(+-)-Camphor;
EINECS:	200-945-0
Density:	0.982 g/cm³
Melting Point:	179 °C
Boiling Point:	207.4 °C at 760 mmHg
Flash Point:	64.4 °C
Solubility:	0.12 g/100 mL (25 °C) in water
Appearance:	Colourless solid
Hazard Symbols:	F, Xn, Xi
Risk Codes:	11-22-36/37/38-20/21/22
Safety:	16-26-37/39
Transport Information:	UN 2717 4.1/PG 3
PSA:	17.07000
LogP:	2.40170

Synthetic route

: 6627-72-1
rac-endo-borneol

: 76-22-2
Camphor

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; chromium tetra(tert-butoxide) In benzene at 20℃; for 24h;	100%
With peracetic acid; 2,4-dimethyl-2,4-pentanediol cyclic Cr(VI) ester In tetrachloromethane; dichloromethane at 0℃; for 12h;	99%
With dimethyl sulfoxide; triethylamine; trichloromethyl chloroformate In dichloromethane	92%

: 124-76-5, 464-43-7, 464-45-9, 507-70-0, 6627-72-1, 10334-13-1, 10385-78-1, 16725-71-6, 24393-70-2
1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

: 76-22-2
Camphor

Conditions

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 3-[4'-(diacetoxyiodo)phenoxy]-1-propyl-N,N,N-trimethylammonium 4-methylbenzenesulfonate In dichloromethane at 20℃; for 12h;	99%
With aluminum oxide; sodium bromite In dichloromethane for 24h; Ambient temperature;	98%
With phosphomolybdic acid; oxygen; tetrabutylammonium acetate; palladium diacetate In toluene at 100℃; under 22502.3 Torr; for 16h; Solvent; Time;	96%
With 1-methyl-1H-imidazole; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 4,4'-Dimethoxy-2,2'-bipyridin; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen In acetonitrile at 70℃; for 1h;	77%
With sodium dichromate; sulfuric acid for 3h; Heating;	55.6%

: 24393-70-2
isoborneol

: 76-22-2
Camphor

Conditions

Conditions	Yield
With bis-trimethylsilanyl peroxide; dipyridinium dichromate In dichloromethane for 0.5h;	98%
With dihydrogen peroxide; methyltrioctylammonium tetrakis(oxodiperoxotungsto)phosphate In 1,1,2,2-tetrachloroethylene at 90℃; for 0.75h;	95%
With oxalyl dichloride; C4F9CH2CH2S(O)CH3 In dichloromethane at -30℃; Swern oxidation;	94%

: 6787-91-3
camphor ethanedithioketal

: 76-22-2
Camphor

Conditions

Conditions	Yield
With ammonium iodide; dihydrogen peroxide; acetic acid In water at 20℃; for 1h;	95%

: 4581-48-0, 10281-41-1, 72059-63-3, 120522-07-8, 121702-12-3, 124815-32-3
bornan-2-one semicarbazone

: 76-22-2
Camphor

Conditions

Conditions	Yield
With tetraethylammonium bromate In ethanol for 3h; Heating;	92%
With potassium permanganate; silica gel In water at 20℃; for 0.5h;	80%

: 18674-50-5
camphor oxime

: 76-22-2
Camphor

Conditions

Conditions	Yield
With dibromamine-B In tetrachloromethane at 20 - 25℃; for 0.333333h;	90%
With N-iodo-succinimide; water In acetone for 0.05h; Microwave irradiation;	87%
With water; oxygen In acetonitrile at 60℃; under 760.051 Torr; for 6h; Autoclave; Green chemistry;	83%
With Oxone; silica gel In water; acetic acid at 25℃; for 24h;	57%

: 18529-99-2, 75524-60-6
1-bornenyl acetate

: 76-22-2
Camphor

Conditions

Conditions	Yield
With water; dichloro bis(acetonitrile) palladium(II) In isopropyl alcohol at 80℃; for 24h;	87%

: 76-29-9, 1925-58-2, 10293-06-8, 27799-07-1, 55057-87-9, 64474-54-0, 67337-12-6, 107870-25-7
3-bromo-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

: 76-22-2
Camphor

Conditions

Conditions	Yield
With sodium hydrogen telluride In ethyl acetate for 1h; Ambient temperature;	78%

: 76-29-9
3-exo-Bromocamphor

: 76-22-2
Camphor

Conditions

Conditions	Yield
With water; zinc In acetonitrile at 80℃; for 11h; Inert atmosphere; Sealed tube;	76%
With Methyltrichlorosilane; sodium iodide In acetonitrile for 18h; Heating;	60%

: 1,7,7-trimethyl-2-nitrobicyclo[2.2.1]heptane

: 76-22-2
Camphor

Conditions

Conditions	Yield
Stage #1: 1,7,7-trimethyl-2-nitrobicyclo[2.2.1]heptane With potassium hydride In 1,4-dioxane at 10℃; for 1h; Stage #2: With chloro-trimethyl-silane In 1,4-dioxane for 15h; Nef reaction; Heating; Further stages.;	62%

Raw Materials

464-43-7

Downstream Products

108-39-4

7647-01-0

110-16-7

464-45-9

563-80-4

79-92-5

4501-58-0

535-77-3

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History

In the 9th century, the Arab chemist, Al-Kindi, provided the earliest recipe for the production of camphor in his Kitab Kimiya' al-'Itr.
Already in the 19th century, it was known that with nitric acid, camphor could be oxidized into camphoric acid. Haller and Blanc published a semisynthesis of camphor from camphoric acid, which, although demonstrating its structure, would not prove it. In 1903,the first complete total synthesis for camphoric acid was published by Gustaf Komppa.
In 1907, Komppa began industrial production of camphor in Tainionkoski, Finland.

Standards and Recommendations

OSHA PEL: TWA 2 mg/m³
ACGIH TLV: TWA 2 ppm; STEL 3 ppm; Not Classifiable as a Human Carcinogen
DFG MAK: 2 ppm (13 mg/m³)
DOT Classification: 4.2; Label: Flammable Solid

Analytical Methods

For occupational chemical analysis use NIOSH: Ketones II (desorption in 99:1 CS₂:methanol) 1301.

Specification

The Camphor with CAS registry number of 76-22-2 is also known as Norcamphor, 1,7,7-trimethyl-. The IUPAC name is 4,7,7-Trimethylbicyclo[2.2.1]heptan-3-one. It belongs to product categories of Fine Chemical & Intermediates; Miscellaneous Natural Products; Ketone; Bicyclic Monoterpenes; Biochemistry; Camphor, etc. (Plasticizer); Functional Materials; Plasticizer; Terpenes. Its EINECS registry number is 200-945-0. In addition, the formula is C₁₀H₁₆O and the molecular weight is 152.23. This chemical is a colourless solid and should be stored in cool and dry place.

Physical properties about Camphor are: (1)ACD/LogP: 2.13; (2)ACD/LogD (pH 5.5): 2.13; (3)ACD/LogD (pH 7.4): 2.13; (4)ACD/BCF (pH 5.5): 24.39; (5)ACD/BCF (pH 7.4): 24.39; (6)ACD/KOC (pH 5.5): 342.47; (7)ACD/KOC (pH 7.4): 342.47; (8)#H bond acceptors: 1; (9)Index of Refraction: 1.485; (10)Molar Refractivity: 44.39 cm³; (11)Molar Volume: 154.8 cm³; (12)Surface Tension: 31.5 dyne/cm; (13)Density: 0.982 g/cm³; (14)Flash Point: 64.4 °C; (15)Enthalpy of Vaporization: 44.37 kJ/mol; (16)Boiling Point: 207.4 °C at 760 mmHg; (17)Vapour Pressure: 0.225 mmHg at 25 °C.

Preparation of Camphor: it is prepared by reaction of Turpentine. Camphene is obtained by the isomerization after pinene extraction. Then product is obtained by esterification, hydrolysis and dehydrogenation of camphen.

Uses of Camphor: it is used as chemical-based raw material and pharmaceutical intermediate. It is used to produce camphor-trimethylsilyl-enolether by reaction with chloro-trimethyl-silane. The reaction occurs with reagents NaI, triethylamine and solvents acetonitrile, pentane at ambient temperature for 96 hoursfor hours. The yield is about 59%.

Camphor is used to produce camphor-trimethylsilyl-enolether by reaction with chloro-trimethyl-silane.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. It is harmful by inhalation, in contact with skin and if swallowed. What's more, it is highly flammable. During using it, wear suitable protective clothing and eye/face protection. Keep away from sources of ignition. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC1(C2CCC1(C(=O)C2)C)C
2. InChI: InChI=1S/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3
3. InChIKey: DSSYKIVIOFKYAU-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LDLo	intraperitoneal	400mg/kg (400mg/kg)		"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
child	LDLo	unreported	100mg/kg (100mg/kg)		Yakkyoku. Pharmacy. Vol. 31, Pg. 1499, 1980.
child	TDLo	oral	51mg/kg (51mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	American Journal of Emergency Medicine. Vol. 7, Pg. 41, 1989.
dog	LDLo	oral	800mg/kg (800mg/kg)		"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
frog	LDLo	subcutaneous	240mg/kg (240mg/kg)	PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE	Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 50, Pg. 199, 1903.
infant	LDLo	oral	70mg/kg (70mg/kg)	SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS	American Journal of Pathology. Vol. 30, Pg. 857, 1954.
man	LDLo	unreported	29mg/kg (29mg/kg)		"Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse	LCLo	inhalation	400mg/m³/3H (400mg/m3)	BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 22(11), Pg. 83, 1957.
mouse	LD50	intraperitoneal	3gm/kg (3000mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: REGIDITY BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	American Journal of Pathology. Vol. 30, Pg. 857, 1954.
mouse	LD50	oral	1310mg/kg (1310mg/kg)		Shika Gakuho. Journal of Dentistry. Vol. 75, Pg. 934, 1975.
mouse	LDLo	subcutaneous	200mg/kg (200mg/kg)	BEHAVIORAL: EXCITEMENT	"Pharmakologische Prufung von Analgetika, Dissertation," Herrlen, G., Pharmakologischen Institut der Universitat Tubingen, Fed. Rep. Ger., 1933Vol. -, Pg. -, 1933.
rabbit	LDLo	oral	2gm/kg (2000mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: REGIDITY	American Journal of Pathology. Vol. 30, Pg. 857, 1954.
rat	LD50	subcutaneous	70mg/kg (70mg/kg)		"Ueber die Pharmakologische Wirkung eines dem Pentamethylentetrazol Vol. -, Pg. -, 1934.
rat	LDLo	intraperitoneal	900mg/kg (900mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Journal of Pharmacology and Experimental Therapeutics. Vol. 65, Pg. 275, 1939.