2-Nitrobenzyl bromide

Base Information

• Chemical Name: 2-Nitrobenzyl bromide
• CAS No.: 3958-60-9
• Molecular Formula: C7H6BrNO2
• Molecular Weight: 216.034
• Hs Code.: 29049085
• European Community (EC) Number: 223-558-9
• NSC Number: 95415
• DSSTox Substance ID: DTXSID80192699
• Nikkaji Number: J29.537J
• Wikidata: Q72494473
• ChEMBL ID: CHEMBL172430
• Mol file: 3958-60-9.mol

Synonyms:2-Nitrobenzyl bromide;3958-60-9;1-(Bromomethyl)-2-nitrobenzene;o-Nitrobenzyl bromide;alpha-Bromo-2-nitrotoluene;2-(Bromomethyl)nitrobenzene;2-Nitrobenzylbromide;1-(Bromomethyl)-2-nitro-benzene;Benzene, bromomethylnitro-;Benzene, 1-(bromomethyl)-2-nitro-;CCRIS 7966;2-nitro benzyl bromide;EINECS 223-558-9;NSC 95415;o-Nitrobenayl bromide;2-nitro-benzyl bromide;1-Bromomethyl-2-nitrobenzene;o-nitrobenzylbromide;MFCD00007184;ortho-nitrobenzylbromide;a-Bromo-2-nitrotoluene;2-bromomethyl-nitrobenzene;SCHEMBL70062;2-Nitrobenzyl bromide, 98%;1-Bromomethyl-2-nitro-benzene;CHEMBL172430;DTXSID80192699;1-(Bromomethyl)-2-nitrobenzene #;NSC95415;CX1355;NSC-95415;STK498198;AKOS000476487;CS-W002026;GS-3305;UPCMLD0ENAT5408169:001;AC-25716;BP-12500;LS-188317;AM20040373;FT-0613187;N0404;EN300-10621;A22364;o-Nitrobenaylbromide;W-106418;Z56347373;F8881-5747;METHYL4-(1-HYDROXYIMINOETHYL)-5-METHYLISOXAZOLE-3-CARBOXYLATE

Chemical Property of 2-Nitrobenzyl bromide

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00868mmHg at 25°C
• Melting Point: 44-46 °C(lit.)
• Refractive Index: 1.611
• Boiling Point: 275.2 °C at 760 mmHg
• Flash Point: 120.2 °C
• PSA: 45.82000
• Density: 1.652 g/cm³
• LogP: 3.01290
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: insoluble
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 214.95819
• Heavy Atom Count: 11
• Complexity: 146

Purity/Quality:

99% ^*data from raw suppliers

2-Nitrobenzyl bromide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CBr)[N+](=O)[O-]
• Uses: 2-Nitrobenzyl bromide is used in the preparation of S-2-nitrobenzyl-cysteine by reaction with L-cysteine. It is also used for the introduction of the 2-nitrobenzyl protecting group in organic synthesis. It plays an important role in the production of expectorant agent. Further, it is employed for caging unprotected cysteine-containing or thiophosphorylated peptides in aqueous solution. In addition to this, it is used in the preparation of (R)- and (S)-3-amino-3,4-dihydro-1H-quinolin-2-one. 2-Nitrobenzyl bromide was used for caging unprotected cysteine-containing or thiophosphorylated peptides in aqueous solution. It can be used in the synthesis of (R)- and (S)-3-amino-3,4-dihydro-1H-quinolin-2-one.

Technology Process of 2-Nitrobenzyl bromide

There total 13 articles about 2-Nitrobenzyl bromide 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%

1-methyl-2-nitrobenzene (88-72-2) → 2-nitrophenylmethyl bromide (3958-60-9)

Guidance literature:

With dihydrogen peroxide; bromine; In dichloromethane; water; for 4h; Reflux;

Reference yield: 97.0%

2-Nitrobenzyl alcohol (612-25-9) → 2-nitrophenylmethyl bromide (3958-60-9)

Guidance literature:

With 4-aminophenyl diphenylphosphinite; bromine; In dichloromethane; at 20 ℃; for 0.416667h;

DOI:10.1139/V06-120

Reference yield: 95.1%

1-(methoxymethyl)-2-nitrobenzene (38177-30-9) → 2-nitrophenylmethyl bromide (3958-60-9)

Guidance literature:

With hydrogen bromide; acetic acid; at 65 ℃; for 2h; Inert atmosphere;

upstream raw materials:

tetrachloromethane

N-Bromosuccinimide

1-methyl-2-nitrobenzene

dibenzoyl peroxide

Downstream raw materials:

1-(2-nitro-benzyloxy)-pyridinium; bromide

4-(2-amino-thiobenzoyl)-morpholine

4-(2-nitro-thiobenzoyl)-morpholine

1-(2-nitrobenzyl)-1H-imidazole

Refernces

• 1、 Mekonnen Sanka, Bruktawit,Mamo Tadesse, Dereje,Teju Bedada, Endale,Mengesha, Ephriem T.,Babu G., Neelaiah. "Design, synthesis, biological screening and molecular docking studies of novel multifunctional 1,4-di (aryl/heteroaryl) substituted piperazine derivatives as potential antitubercular and antimicrobial agents". . . Retrieved 2022/01/20.
• 2、 Lu, Guan-Han,Huang, Tzu-Chia,Hsueh, Hsiao-Chin,Yang, Shin-Cherng,Cho, Ting-Wei,Chou, Ho-Hsuan. "NovelN-transfer reagent for converting α-amino acid derivatives to α-diazo compounds". supporting information. p. 4839 - 4842. Retrieved 2021/05/25.