2-Aminobenzaldehyde

Base Information

• Chemical Name: 2-Aminobenzaldehyde
• CAS No.: 529-23-7
• Molecular Formula: C7H7NO
• Molecular Weight: 121.139
• Hs Code.: 29223990
• European Community (EC) Number: 208-454-3
• UNII: EG769PG2AX
• DSSTox Substance ID: DTXSID6060183
• Nikkaji Number: J6.682F,J662.592D
• Wikipedia: 2-Aminobenzaldehyde
• Wikidata: Q21099244
• Mol file: 529-23-7.mol

Synonyms:2-aminobenzaldehyde;o-aminobenzaldehyde;ortho aminobenzaldehyde

Chemical Property of 2-Aminobenzaldehyde

Chemical Property:

• Appearance/Colour: light yellow crystalline powder
• Vapor Pressure: 0.0135mmHg at 25°C
• Melting Point: 38 °C
• Refractive Index: 1.639
• Boiling Point: 258.7 °C at 760 mmHg
• PKA: -0.01±0.10(Predicted)
• Flash Point: 110.2 °C
• PSA: 43.09000
• Density: 1.171 g/cm³
• LogP: 1.66250
• Storage Temp.: −20°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 121.052763847
• Heavy Atom Count: 9
• Complexity: 103

Purity/Quality:

99.9% ^*data from raw suppliers

2-Aminobenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C=O)N
• Description: 2-Aminobenzaldehyde is one of the three isomers of aminobenzaldehyde. It is used as a versatile substrate for rhodium-catalyzed alkyne hydroacylation.1 It is used to prepare quinoline derivatives as antiviral agents, electroluminescent materials for OLEDs, and 2-tosylaminopheyl cyclopropylmethanols for gold-catalyzed cyclopropyl carbinol rearrangement. It is also used for the Friedl?nder-type synthesis, the benzyl C-H bond amination of acrymethylamines catalyzed by hydroxy-TEMPO, and for silver-catalyzed aniline mediated cascade hydroamination/cycloaddition reactions.
• Physical properties: 2-Aminobenzaldehyde has recently been identifed as an important component in the fragrant scents of many flowers. These flowers include broom (Spartium junceum), false acacia (Robinia pseudoacacia), European bird cherry (Padus avium), ily (Lilium candidum), seringat (Philadelphus coronarius), Pittosporum tobira, Hypecoum imberbe, and H. fragrant. This chemical is also responsible for the“"sweet" or fragrant odor of the wild mushroom Hebeloma sacchariolens.
• Uses: Reactant for: Preparation of quinoline derivatives as antiviral agents Preparation of electroluminescent materials for OLEDs Friedlander-type synthesis Preparation of 2-tosylaminophenyl cyclopropylmethanols for gold-catalyzed cyclopropyl carbinol rearrangement Benzyl C-H bond amination of arylmethylamines catalyzed by hydroxy-TEMPO Silver-catalyzed aniline mediated cascade hydroamination/cycloaddition reactions Reactant for:Preparation of quinoline derivatives as antiviral agentsPreparation of electroluminescent materials for OLEDsFriedlander-type synthesisPreparation of 2-tosylaminophenyl cyclopropylmethanols for gold-catalyzed cyclopropyl carbinol rearrangementBenzyl C-H bond amination of arylmethylamines catalyzed by hydroxy-TEMPOSilver-catalyzed aniline mediated cascade hydroamination/cycloaddition reactions

Technology Process of 2-Aminobenzaldehyde

There total 103 articles about 2-Aminobenzaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-Aminobenzyl alcohol (5344-90-1) → o-aminobenzaldehyde (529-23-7)

Guidance literature:

With hydrotalcite; RuMn₂; oxygen; In toluene; at 60 ℃; for 21h; atmospheric pressure;

DOI:10.1002/anie.200462600

Reference yield: 95.9%

1-methyl-2-nitrobenzene (88-72-2) → o-aminobenzaldehyde (529-23-7)

Guidance literature:

With 2,3,4,5,7,8,9,10-octahydropyrimido[1,2-a]azepin-1-ium acetate; In methanol; at 60 ℃; for 3h; Temperature; Solvent;

Reference yield: 71.9%

2-aminophenethyl alcohol (5339-85-5) → o-aminobenzaldehyde (529-23-7)

Guidance literature:

With dmap; pyridinium chlorochromate; In dichloromethane; at 0 - 20 ℃; for 5h;

DOI:10.1016/j.bmc.2014.02.053

upstream raw materials:

2-Nitrobenzyl alcohol

sodium ethanolate

2-aminobenzaldehyde oxime

anthranil

Downstream raw materials:

2,3-trimethylene-1,2-dihydroquinazolinium picrate

4-((2-formylphenyl)amino)-4-oxobutanoic acid

2-hydroxymethylquinoline-3-carboxylic acid lactone

2-amino-benzaldehyde-(4-methyl-6-oxo-1,6-dihydro-pyrimidin-2-ylhydrazone)

Refernces

• 1、 Lone, Shabir H.,Jameel, Salman,Bhat, Muzzaffar A.,Lone, Rayees A.,Butcher, Ray J.,Bhat, Khursheed A.. "Synthesis of an unusual quinazoline alkaloid: Theoretical and experimental investigations of its structural, electronic, molecular and biological properties". . p. 8259 - 8268. Retrieved 2018.
• 2、 Hirahara, Masanari,Tsukamoto, Akira,Goto, Hiroki,Tada, Shigeru,Yagi, Masayuki,Umemura, Yasushi. "Visible-Light-Induced Morphological Changes of Giant Vesicles by Photoisomerization of a Ruthenium Aqua Complex". . p. 2590 - 2594. Retrieved 2016.
• 3、 Wang, Haishan,Ganesan. "Total synthesis of the cytotoxic alkaloid luotonin A". . p. 9097 - 9098. Retrieved 1998.
• 4、 Zhuang, Shi-Yi,Tang, Yong-Xing,He, Cai,Chen, Xiang-Long,Xue, Wei-Jian,Wu, Yan-Dong,Wu, An-Xin. "Copper-catalyzed Reaction of Anthranils with Methyl Ketones: Site-Selective C5-Dicarbonylation of Anthranils". . p. 1137 - 1141. Retrieved 2021.
• 5、 Che, Jinxin,Ma, Canliang,Lu, Jialiang,Chen, Binhui,Shi, Qiuqiu,Jin, Xinxin,Song, Rui,Xu, Fan,Gan, Lishe,Li, Jingya,Hu, Yongzhou,Dong, Xiaowu. "Discovery of seneciobipyrrolidine derivatives for the amelioration of glucose homeostasis disorders through 4E-BP1/Akt/AMPK signaling activation". . . Retrieved 2021/11/16.
• 6、 Mao, Kaining,Nutting, Jordan E.,Stahl, Shannon S.. "Iron(III) Nitrate/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Distinguishing between Serial versus Integrated Redox Cooperativity". supporting information. p. 10565 - 10570. Retrieved 2021/07/28.