4-Nitrobenzyl chloride

Base Information

• Chemical Name: 4-Nitrobenzyl chloride
• CAS No.: 100-14-1
• Molecular Formula: C7H6ClNO2
• Molecular Weight: 171.583
• Hs Code.: 29049090
• European Community (EC) Number: 202-822-7
• NSC Number: 9803
• UN Number: 3261
• UNII: 3BLD9LVT3X
• DSSTox Substance ID: DTXSID4025745
• Nikkaji Number: J4.978F
• Wikidata: Q27159602
• ChEMBL ID: CHEMBL176410
• Mol file: 100-14-1.mol

Synonyms:4-nitrobenzyl chloride;p-nitrobenzyl chloride;para-nitrobenzyl chloride

Chemical Property of 4-Nitrobenzyl chloride

Chemical Property:

• Appearance/Colour: Light yellow crystalline powder
• Vapor Pressure: 0.0995mmHg at 25°C
• Melting Point: 71 °C
• Refractive Index: 1.574
• Boiling Point: 292.515 °C at 760 mmHg
• Flash Point: 130.709 °C
• PSA: 45.82000
• Density: 1.33 g/cm³
• LogP: 2.85680
• Solubility.: chloroform: soluble50mg/mL, clear to very slightly hazy, faintly
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 171.0087061
• Heavy Atom Count: 11
• Complexity: 138
• Transport DOT Label: Corrosive

Purity/Quality:

99% ^*data from raw suppliers

4-Nitrobenzyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 22-34-36
• Safety Statements: 26-36/37/39-45-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitros, Aromatic
• Canonical SMILES: C1=CC(=CC=C1CCl)[N+](=O)[O-]
• Uses: 4-Nitrobenzyl chloride was used to prepare unsymmetrically N,N′-bis(substituted) 4,13-diaza-18-crown-6-ether derivatives.

Technology Process of 4-Nitrobenzyl chloride

There total 45 articles about 4-Nitrobenzyl chloride 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: 95.0%

benzyl chloride (100-44-7) → 4-nitrobenzyl chloride (100-14-1)

Guidance literature:

With sulfuric acid; silica gel; tetramethylammonium nitrate; for 0.0333333h;

DOI:10.1080/00397910500184685

Reference yield: 82.0%

1-methyl-4-nitrobenzene (99-99-0) → 4-nitrobenzyl chloride (100-14-1)

Guidance literature:

With hydrogenchloride; potassium chloride; tetrabutyl-ammonium chloride; In water; at 20 ℃; Irradiation; Green chemistry;

DOI:10.1039/c8gc02628a

Reference yield: 43.0%

4-nitrobenzyl chloride (619-73-8) → 4-nitrobenzaldehdye (555-16-8) + 4-nitrobenzyl chloride (100-14-1)

Guidance literature:

With 2-chloro-1,3-dimethylimidazolinium chloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/jo990211q

upstream raw materials:

4-nitrobenzyl chloride

1-methyl-4-nitrobenzene

hexabromobenzene

4-nitrobenzyl fluoride

Downstream raw materials:

1,3-bis-(4-nitro-benzyl)-imidazolium; chloride

2-methyl-1-(4-nitrobenzyl)pyridinium chloride

4-methyl-3-(4-nitro-benzyl)-thiazolium; chloride

2-(4-nitro-benzyl)-isoquinolinium; chloride

Refernces

• 1、 Yasuda, Makoto,Yamasaki, Satoshi,Onishi, Yoshiyuki,Baba, Akio. "Indium-catalyzed direct chlorination of alcohols using chlorodimethylsilane-benzil as a selective and mild system". . p. 7186 - 7187. Retrieved 2004.
• 2、 Khutorianskyi, Viktor V.,Klepetá?ová, Blanka,Beier. "Vicarious Nucleophilic Chloromethylation of Nitroaromatics". . p. 5443 - 5446. Retrieved 2019.
• 3、 Hussein, Mohanad A.,Nguyen, Thanh Vinh. "Promotion of Appel-type reactions by N-heterocyclic carbenes". . p. 7962 - 7965. Retrieved 2019.
• 4、 Yu, Jia,Li, Minglei,Yu, Yong,Gao, Yanjing,Liu, Jiancheng,Sun, Fang. "Synthetic Strategy and Performances of a UV-Curable Poly Acryloyl Phosphinate Flame Retardant by Carbene Polymerization". . p. 1958 - 1970. Retrieved 2015.
• 5、 Sakai, Norio,Nakajima, Takumi,Yoneda, Shinichiro,Konakahara, Takeo,Ogiwara, Yohei. "Gallium-catalyzed reductive chlorination of carboxylic acids with copper(II) chloride". . p. 10619 - 10623. Retrieved 2014.
• 6、 Zheng, Dagui,Mao, Liu-Liang,Zhu, Xian-Hong,Zhou, An-Xi. "NMP-mediated chlorination of aliphatic alcohols with aryl sulfonyl chloride for the synthesis of alkyl chlorides". . p. 2793 - 2800. Retrieved 2018.
• 7、 Knowles,Norman. "-". . p. 3888. Retrieved 1961.
• 8、 Liu, Shouxin,Zhang, Qi,Tian, Xia,Fan, Shiming,Huang, Jing,Whiting, Andrew. "Highly selective halogenation of unactivated C(sp3)-H with NaX under co-catalysis of visible light and Ag@AgX". . p. 4729 - 4737. Retrieved 2018.
• 9、 Moss, Robert A.,Ma, Yan,Sauers, Ronald R.. "A duality of mechanisms for the fragmentation of substituted benzyloxychlorocarbenes". . p. 13968 - 13969. Retrieved 2002.
• 10、 Mohite, Amar R.,Phatake, Ravindra S.,Dubey, Pooja,Agbaria, Mohamed,Shames, Alexander I.,Lemcoff, N. Gabriel,Reany, Ofer. "Thiourea-Mediated Halogenation of Alcohols". . p. 12901 - 12911. Retrieved 2020/11/26.