(6-Bromonaphthalen-2-yl)methanol

Base Information

• Chemical Name: (6-Bromonaphthalen-2-yl)methanol
• CAS No.: 100751-63-1
• Molecular Formula: C11H9BrO
• Molecular Weight: 237.096
• DSSTox Substance ID: DTXSID90541715
• Wikidata: Q82418148
• Mol file: 100751-63-1.mol

Synonyms:100751-63-1;(6-Bromonaphthalen-2-yl)methanol;6-Bromo-2-naphthylmethanol;2-Naphthalenemethanol, 6-bromo-;6-bromo-2-naphthalenemethanol;(6-bromo-2-naphthyl)methanol;(6-bromo-naphthalen-2-yl)-methanol;6-BROMO-2-NAPHTHYL METHANOL;MFCD09842470;SCHEMBL1133989;6-bromo-2-naphthylmethyl alcohol;DTXSID90541715;MAARRMBCEFVKNV-UHFFFAOYSA-N;(6-bromonaphthalene-2-yl)methanol;AMY19149;6-bromo-2-(hydroxymethyl)naphthalene;AKOS016007584;AS-60463;SY334958;CS-0046891;F10523;EN300-2943175;Z1269244063

Chemical Property of (6-Bromonaphthalen-2-yl)methanol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 152-153℃
• Boiling Point: 374.611oC at 760 mmHg
• PKA: 14.15±0.10(Predicted)
• Flash Point: 180.359oC
• PSA: 20.23000
• Density: 1.544g/cm3
• LogP: 3.09460
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DCM, DMSO. DMF, Ethyl Acetate
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 235.98368
• Heavy Atom Count: 13
• Complexity: 172

Purity/Quality:

99% ^*data from raw suppliers

6-Bromo-2-naphthalenemethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CC(=C2)Br)C=C1CO
• Uses: 6-Bromo-2-naphthalenemethanol is an intermediate in the synthesis of Adapalene (A225000), an antiacne agent.

Technology Process of (6-Bromonaphthalen-2-yl)methanol

There total 7 articles about (6-Bromonaphthalen-2-yl)methanol 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: 99.0%

methyl 6-bromo-2-naphthoate (33626-98-1) → (6-bromo-2-naphthy)methanol (100751-63-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -10 - -5 ℃; for 1.33333h;

Reference yield: 96.0%

6-bromo-naphthalene-2-carboxaldehyde (170737-46-9) → (6-bromo-2-naphthy)methanol (100751-63-1)

Guidance literature:

With methanol; sodium tetrahydroborate; at 0 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1002/anie.201806742

Reference yield: 90.0%

6-bromo-2-naphthoic acid (5773-80-8) → (6-bromo-2-naphthy)methanol (100751-63-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating;

DOI:10.1016/j.bmcl.2007.10.079

upstream raw materials:

6-bromo-2-naphthoic acid

methyl 6-bromo-2-naphthoate

ethyl 6-bromo-naphthalene-2-carboxylate

6-bromo-naphthalene-2-carboxaldehyde

Downstream raw materials:

6-(hydroxymethyl)-2-naphthonitrile

1-(6-bromonaphthalen-2-yl)ethanone

Refernces

• 1、 Lv, Guanglei,Cui, Baiping,Lan, Haichuang,Wen, Ying,Sun, Anyang,Yi, Tao. "Diarylethene based fluorescent switchable probes for the detection of amyloid-β pathology in Alzheimer's disease". . p. 125 - 128. Retrieved 2015.
• 2、 Hannu-Kuure, Milja,K?rkk?inen, Ari,Legrand, Sacha. "Design, synthesis, and characterization of 6-[(trimethyl)silylethynyl]naphthalene-2-ethene: A new precursor for the preparation of high-refractive-index organic materials". . . Retrieved 2020.
• 3、 Teppang, Kristine L.,Ehrlich, Rachel S.,Yang, Jerry. "Method to discriminate amyloids using fluorescent probes". . p. 91 - 114. Retrieved 2020.
• 4、 Granzhan, Anton,Teulade-Fichou, Marie-Paule. "Synthesis of mono- and bibrachial naphthalene-based macrocycles with pyrene or ferrocene units for anion detection". . p. 1349 - 1360. Retrieved 2009.
• 5、 Pu, Yu-Ming,Ku, Yi-Yin,Grieme, Timothy,Black, Lawrence A.,Bhatia, Ashok V.,Cowart, Marion. "An expedient and multikilogram synthesis of a naphthalenoid H3 antagonist". . p. 1004 - 1009. Retrieved 2007.
• 6、 -. "COMPOSITIONS AND METHODS FOR DETECTION OF TRAUMATIC BRAIN INJURY". . . Retrieved 2021/12/03.