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(R)-3,3'-Dimethyl-1,1'-binaphthalene-2,2'-diol

CAS No.
55515-98-5
Chemical Name:
(R)-3,3'-Dimethyl-1,1'-binaphthalene-2,2'-diol
Synonyms
3,3'-Dimethyl-1,1'-binaphthalene-2-2'-diol;(R)-3,3'-Dimethyl-1,1'-binaphthalene-2,2'-diol;(S)-3,3'-DIMETHYL-1,1'-BINAPHTHALENE-2,2'-DIOL;(1R)-3,3'-diMethyl-1,1'-Binaphthalene]-2,2'-diol;(1R)-3,3'- dimethyl [1,1'- binaphthyl ]-2,2'- diol;[1,1'-Binaphthalene]-2,2'-diol,3,3'-dimethyl-, (1R)-;(R)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol, 99%e.e.;(1R)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol, 98% (99% ee)
CBNumber:
CB3752230
Molecular Formula:
C22H18O2
Molecular Weight:
314.38
MDL Number:
MFCD00187966
MOL File:
55515-98-5.mol
Last updated:2026-09-12 18:52:11

(R)-3,3'-Dimethyl-1,1'-binaphthalene-2,2'-diol Properties

Melting point 201-202 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
Boiling point 461.2±40.0 °C(Predicted)
Density 1.245±0.06 g/cm3(Predicted)
storage temp. 2-8°C, protect from light, stored under nitrogen
pka 8.61±0.50(Predicted)
Appearance Off-white to light yellow Solid

(R)-3,3'-Dimethyl-1,1'-binaphthalene-2,2'-diol price More Price(14)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Strem Chemicals 08-1020 (1R)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol, 98% (99% ee) 98%(99%ee) 55515-98-5 100mg $198 2026-04-30 Buy
aablocks AA00ILPP (R)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol 98% 55515-98-5 100mg $23 2026-05-29 Buy
aablocks AA00ILPP (R)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol 98% 55515-98-5 250mg $53 2026-05-29 Buy
aablocks AA00ILPP (R)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol 98% 55515-98-5 1g $166 2026-05-29 Buy
aablocks AA00ILPP (R)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol 98% 55515-98-5 5g $547 2026-05-29 Buy
Product number Packaging Price Buy
08-1020 100mg $198 Buy
AA00ILPP 100mg $23 Buy
AA00ILPP 250mg $53 Buy
AA00ILPP 1g $166 Buy
AA00ILPP 5g $547 Buy

(R)-3,3'-Dimethyl-1,1'-binaphthalene-2,2'-diol Chemical Properties, Uses, Production

Definition

ChEBI: 3,3'-Dimethyl-1,1'-binaphthalene-2,2'-diol is a member of naphthols.

Synthesis

(R)-(+)-2,2'-BIS(METHOXYMETHOXY)-1,1'-BINAPHTHYL

173831-50-0

Dimethyl sulfate

77-78-1

(R)-3,3'-DIMETHYL-1,1'-BINAPHTHALENE-2,2'-DIOL

55515-98-5

The general procedure for the synthesis of (R)-3,3'-dimethyl-[1,1'-binaphthyl]-2,2'-diols from (R)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl and dimethyl sulfate was as follows: firstly, 18.3 g of sodium hydride was mixed with 50 g (0.175 mol) of (R)- 2,2'-dihydroxy-1,1'-binaphthyl suspended in 1.0 L of anhydrous tetrahydrofuran (THF) under nitrogen protection and stirred for 1 hour. Subsequently, 116 g of chloromethyl methyl ether was added to the reaction system and stirring was continued for about 12 hours. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad. The filtrate was subsequently mixed with 500 ml of water and 1 L of dichloromethane for liquid-liquid extraction. After separation of the aqueous layer, the aqueous layer was subjected to a secondary extraction with dichloromethane. The organic layers were combined, washed with saturated aqueous potassium bicarbonate, dried and filtered through a short column of alumina. The filtrate was evaporated until crystals precipitated and the crude product was purified by silica gel column chromatography (eluent: dichloromethane/hexanes) to give about 53.5 g (63% yield) of (R)-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene with a melting point of 93-94°C. The product was purified by silica gel column chromatography. Next, 171 ml of 1.6 M butyl lithium hexane solution was added dropwise to 41 g of the above bisacetal dissolved in 1 L of tetrahydrofuran and stirred at 0°C for 45 min under nitrogen protection. Subsequently, the reaction system was warmed to 25°C, 25.8 ml of dimethyl sulfate was added and stirring was continued for 12 hours. At the end of the reaction, about 30 ml of saturated aqueous sodium carbonate solution was added and the solvent was evaporated at 50°C under reduced pressure. The residue was dissolved with 300 ml of dichloromethane and washed twice with water. Subsequently, 300 ml of dichloromethane, 300 ml of methanol and 25 ml of concentrated hydrochloric acid were added to the organic phase and the solvent was evaporated after stirring for 3 hours. The resulting yellow product was recrystallized by dichloromethane-hexane and purified by silica gel column chromatography (eluent: dichloromethane/hexane=1:1) to give 29.5 g (86% yield) of (R)-3,3'-dimethyl-[1,1'-binaphthyl]-2,2'-diol with a melting point of 204-206°C. 1H NMR (CDCl3) δ: 2.2 (s, 6H) , 7.1 (d, 2H), 7.3 (m, 2H), 7.4 (m, 2H), 7.8 (m, 4H).

References

[1] Patent: US6686479, 2004, B2. Location in patent: Page column 10; 11

(R)-3,3'-Dimethyl-1,1'-binaphthalene-2,2'-diol Preparation Products And Raw materials

Global Suppliers ( 44)
Supplier Tel Email Country ProdList Advantage
Daicel Chiral Technologies (China)CO.,LTD 021-50460086-9 15921403865 han_yajun@dctc.daicel.com China 7909 65
Tianjin Derchemist Science & Technology Co., Ltd. 22-58627059 13920586291 zdcomcon@126.com China 4094 50
Jiangsu Aikon Biopharmaceutical R&D co.,Ltd. 025-66028182 17714375163 yftan@aikonchem.com China 16674 50
Shanghai Chiral bio-compound co., Ltd. 021-5068 3667/17749785980/1029026415; 17749785980 1029026415@qq.com China 4501 58
Shanghai YuanYe Biotechnology Co., Ltd. 15026964105 2881489226@qq.com China 89667 60
Amadis Chemical Company Limited 571-89925085 sales@amadischem.com China 131885 58
Greenherbs Science and Technology Development Co., Ltd. 010-61136123 pub02@greenherbs.com.cn China 4045 58
Henan Alfachem Co.,Ltd. 0371-55051623 18137891487 3983243027@qq.com China 9970 58
Shanghai Anyinuo Biomedical Technology Co., Ltd. 021-34625901 420970979@qq.com China 5978 58
Jiangsu aikang biomedical research and development co., LTD 025-58859352 17714375163 qzhang@aikonchem.com China 15525 58

View Latest Price from (R)-3,3'-Dimethyl-1,1'-binaphthalene-2,2'-diol manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
(R)-3,3'-DIMETHYL-1,1'-BINAPHTHALENE-2,2'-DIOL pictures 2019-09-02 (R)-3,3'-DIMETHYL-1,1'-BINAPHTHALENE-2,2'-DIOL
55515-98-5
$1.00 1KG 98% 1lg; 2kg; 5kg; 10kg; 100kg Career Henan Chemical Co
(S)-3,3'-DIMETHYL-1,1'-BINAPHTHALENE-2,2'-DIOL 3,3'-Dimethyl-1,1'-binaphthalene-2-2'-diol (1R)-3,3'-diMethyl-1,1'-Binaphthalene]-2,2'-diol (R)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol, 99%e.e. (1R)-3,3'-Dimethyl-[1,1'-binaphthalene]-2,2'-diol, 98% (99% ee) [1,1'-Binaphthalene]-2,2'-diol,3,3'-dimethyl-, (1R)- (1R)-3,3'- dimethyl [1,1'- binaphthyl ]-2,2'- diol (R)-3,3'-Dimethyl-1,1'-binaphthalene-2,2'-diol 55515-98-5