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Name	Benz[cd]indol-2(1H)-one	EINECS	204-973-4
CAS No.	130-00-7	Density	1.327 g/cm³
PSA	32.86000	LogP	2.11910
Solubility	N/A	Melting Point	173-178 °C(lit.)
Formula	C₁₁H₇NO	Boiling Point	234.7 °C at 760 mmHg
Molecular Weight	169.183	Flash Point	128.9 °C
Transport Information	N/A	Appearance	light yellow powder
Safety	24/25	Risk Codes	22
Molecular Structure		Hazard Symbols	Xn
Synonyms	Naphthostyril(6CI,7CI);1,8-Naphtholactam;2(1H)-Perinaphthazolone;2(1H)-peri-Naphthazolone;Naphtholactam;	Article Data	63

Benz[cd]indol-2(1H)-one Synthetic route

: 5551-72-4
1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl 4-methylbenzenesulfonate

: 130-00-7
1,8-naphtholactam

Conditions

Conditions	Yield
Stage #1: 1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl 4-methylbenzenesulfonate With sodium hydroxide In ethanol; water for 3h; Reflux; Stage #2: With hydrogenchloride In water at 75℃; Stage #3: In ethanol; water for 3h; Reflux;	94%
With sodium hydroxide In ethanol; water at 20℃; for 3h; Reflux;	83%
With sodium hydroxide In ethanol; water for 3h; Reflux;	83%
Stage #1: 1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl 4-methylbenzenesulfonate With sodium hydroxide In ethanol; water for 3h; Reflux; Stage #2: With hydrogenchloride In ethanol; water at 20℃; for 0.5h;	82%
With water; sodium hydroxide In ethanol for 3h; Reflux;	82%

: 7797-81-1
N-hydroxy-1,8-naphthalenedicarboximide

: 130-00-7
1,8-naphtholactam

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water for 3h; Reflux;	94%
With sodium hydroxide In water for 2h; Reflux;	91.7%
With p-toluenesulfonyl chloride for 1h; Heating;	1.38 g
Multi-step reaction with 2 steps 1.1: 1 h / 95 °C 2.1: sodium hydroxide / ethanol; water / 3 h / Reflux 2.2: 0.5 h / 20 °C View Scheme

: 81-84-5
1,8-Naphthalic anhydride

: 130-00-7
1,8-naphtholactam

Conditions

Conditions	Yield
Stage #1: 1,8-Naphthalic anhydride With hydroxylamine hydrochloride In pyridine for 1h; Heating; Stage #2: With p-toluenesulfonyl chloride In pyridine for 1h; Heating; Further stages.;	91%
With hydroxylamine; p-toluenesulfonyl chloride In pyridine Beckmann rearrangement;	64%
Multi-step reaction with 2 steps 1.1: hydroxylamine hydrochloride; pyridine / 1 h / Reflux 1.2: 1 h / 80 °C / Reflux 2.1: sodium hydroxide / ethanol; water / 3 h / Reflux 2.2: 75 °C 2.3: 3 h / Reflux View Scheme

: (Z)-2-benzylidene-1,2-dihydrobenzo[cd]indole

: 130-00-7
1,8-naphtholactam

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 2h;	87%

: 95-50-1
1,2-dichloro-benzene

: 86-84-0
1-Naphthyl isocyanate

: 130-00-7
1,8-naphtholactam

Conditions

Conditions	Yield
AlCl3 In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water	80%

: N-(8-(2-oxo-2-phenylethyl)naphthalen-1-yl)quinoline-2-carboxamide

: 130-00-7
1,8-naphtholactam

Conditions

Conditions	Yield
With lithium hydroxide monohydrate; dihydrogen peroxide In tetrahydrofuran; water at 0 - 20℃; for 24h;	80%

: 320582-41-0
N-(1-naphthalen-1-yl)pyrazine-2-carboxamide

: benzene 1,3,5-triyl triformate

: 130-00-7
1,8-naphtholactam

Conditions

Conditions	Yield
With triethylamine; silver carbonate; cobalt(II) chloride; Trimethylacetic acid In 1,4-dioxane at 130℃; for 20h; Inert atmosphere; Sealed tube;	47%

: 2216-13-9
8-nitro-1-naphthalenecarboxylic acid

: 64-19-7
acetic acid

A: 130-00-7
1,8-naphtholactam

B: 1384846-98-3
2-methylnaphtho[1,2-d]oxazole-9-carboxylic acid

C: 1384846-99-4
2-oxo-1,2-dihydrobenzo[c,d]indol-6-yl acetate

Conditions

Conditions	Yield
With zinc for 1h; Reflux;	A 46% B 12% C 27%

: 81-83-4
1,8-Naphthalimide

: 130-00-7
1,8-naphtholactam

Conditions

Conditions	Yield
With sodium hydroxide; sodium hypochlorite
Multi-step reaction with 2 steps 1: aqueous NaOH; NaClO 2: NaOH-solution; water / und Erhitzen der Reaktionsloesung mit Essigsaeure View Scheme

: 64-17-5
ethanol

: 129-02-2
8-amino-[1]naphthoic acid

: 130-00-7
1,8-naphtholactam

Benz[cd]indol-2(1H)-one Chemical Properties

Molecular Structure of Benz[cd]indol-2(1H)-one (CAS NO.130-00-7):

Chemical Name: Benz[cd]indol-2(1H)-one
CAS No.: 130-00-7
EINECS: 204-973-4
RTECS: DE3202000
Molecular Formula: C₁₁H₇NO
Molecular Weight: 169.18 g/mol
Melting Point: 173-178 °C(lit.)
Density: 1.327 g/cm³
Flash Point: 128.9 °C
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 0
Polar Surface Area: 20.31Å²
Index of Refraction: 1.723
Molar Refractivity: 50.52 cm³
Molar Volume: 127.4 cm³
Surface Tension: 57.3 dyne/cm
Enthalpy of Vaporization: 47.15 kJ/mol
Vapour Pressure: 0.0521 mmHg at 25°C
Boiling Point: 234.7 °C at 760 mmHg
InChI
InChI=1/C11H7NO/c13-11-8-5-1-3-7-4-2-6-9(12-11)10(7)8/h1-6H,(H,12,13)
Smiles
O=C1Nc2c3c(ccc2)cccc13
EINECS: 204-973-4
Product Categories: Intermediates of Dyes and Pigments; Fused Ring Systems; Building Blocks; Heterocyclic Building Blocks; Indoles

Benz[cd]indol-2(1H)-one Production

Product Categories about 1,8-NAPHTHOLACTAM (130-00-7) are Intermediates of Dyes and Pigments ; Fused Ring Systems ; Building Blocks ; Heterocyclic Building Blocks ; Indoles

Benz[cd]indol-2(1H)-one Toxicity Data With Reference

mammal (species unspecified)	LD50	oral	2700mg/kg (2700mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(1), Pg. 82, 1986.
mouse	LD50	oral	1gm/kg (1000mg/kg)	BEHAVIORAL: ATAXIA	Collection of Czechoslovak Chemical Communications. Vol. 50, Pg. 1888, 1985.

Benz[cd]indol-2(1H)-one Consensus Reports

Reported in EPA TSCA Inventory.

Benz[cd]indol-2(1H)-one Safety Profile

Moderately toxic by an unspecified route. Slightly toxic by ingestion. When heated to decomposition it emits toxic vapors of NO_x.
Hazard Codes: Harmful Xn
Risk Statements: 22
R22:Harmful if swallowed.
WGK Germany: 2
RTECS: DE3202000

Benz[cd]indol-2(1H)-one Specification

Benz[cd]indol-2(1H)-one , with CAS number of 130-00-7, can be called 1-Naphthalenecarboxylic acid, 8-amino-, lactam ; 1,8-Naphtholactam ; Naphtholactam ; Naftostiril . Benz[cd]indol-2(1H)-one (CAS NO.130-00-7) is mainly used as intermediate for the synthesis of vat dyes and organic pigments.

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